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617-89-0 Usage

Chemical Properties

Furfurylamine is a colorless to light yellow aromatic amine in liquid form with an ammonia odor. Miscible with water, soluble in ethanol, ether. Deteriorates in air by absorbing carbon dioxide. Derived from furfural based on corn cobs, this green chemistry has proven useful in engine cleaners, and as an intermediate for pharmaceutical, industrial and agricultural chemicals.

Uses

Furfurylamine is used as a water miscible solvent and as an intermediate in manufacturing pharmaceuticals like diuretics, antihypertensive, and antiseptic agents.Furfurylamine also has use in the synthesis of Barmastine.2-Furfurylamine is used in the synthesis of 2-Amino-N-(2-furylmethyl)propanamide, as a novel alanylglycine equivalent synthesized by bacilysin synthetase.

Preparation

Synthesis of furfurylamine by Zn/HCl system: To a solution of furfuryloxime (2g, 18mmol) in hydrochloric acid (6.0M, 24ml) was added drop-wise zinc dust (4.71g, 72mmol), and the resultant solution was stirred at room temperature for 2 h. To the resulting slurry was added drop-wise a solution of ammonia (30%, 5.1 mL) and sodium hydroxide (6M, 24mL), the mixture was heated to 60° and stirred for 15mn. After, the resultant solution was cooled and filtered. Then, the mother liquid was extracted with cyclohexane, dried over anhydrous sodium sulfate and filtered. The solvent was removed under vacuum to afford the furfurylamine as a yellow liquid without further purification in 96% of yield (1.68g). The purity determined by NMR was found to be superior to 95%.SIMPLE, NOVEL SYNTHESIS OF FURFURYLAMINE FROM FURFURAL BY ONE-POT REDUCTIVE AMINATION IN WATER USING ZINC METAL

General Description

Furfurylamine appears as a colorless liquid. About the same density as water. Used as a corrosion inhibitor and to make soldering flux.

Air & Water Reactions

Highly flammable. Soluble in water.

Reactivity Profile

Amines, such as Furfurylamine, are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.

Hazard

Flammable, moderate fire risk.

Health Hazard

May cause toxic effects if inhaled or ingested/swallowed. Contact with substance may cause severe burns to skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Fire Hazard

Flammable/combustible material. May be ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

Flammability and Explosibility

Flammable

Safety Profile

Poison by intraperitoneal route. A skin,eye, and mucous membrane irritant. A dangerous fire hazard when exposed to heat or flame; can react with oxidizing materials. To fight fire, use foam, CO2, drp chemical. When heated to decomposition it emits toxic fumes of NOx. See also MINES.

Check Digit Verification of cas no

The CAS Registry Mumber 617-89-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,1 and 7 respectively; the second part has 2 digits, 8 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 617-89:
(5*6)+(4*1)+(3*7)+(2*8)+(1*9)=80
80 % 10 = 0
So 617-89-0 is a valid CAS Registry Number.
InChI:InChI=1/C5H7NO/c6-4-5-2-1-3-7-5/h1-3H,4,6H2/p+1

617-89-0 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
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  • Detail
  • TCI America

  • (F0091)  Furfurylamine  >98.0%(GC)(T)

  • 617-89-0

  • 25mL

  • 105.00CNY

  • Detail
  • TCI America

  • (F0091)  Furfurylamine  >98.0%(GC)(T)

  • 617-89-0

  • 100mL

  • 290.00CNY

  • Detail
  • TCI America

  • (F0091)  Furfurylamine  >98.0%(GC)(T)

  • 617-89-0

  • 500mL

  • 840.00CNY

  • Detail
  • Alfa Aesar

  • (B23975)  Furfurylamine, 99%   

  • 617-89-0

  • 100g

  • 184.0CNY

  • Detail
  • Alfa Aesar

  • (B23975)  Furfurylamine, 99%   

  • 617-89-0

  • 500g

  • 758.0CNY

  • Detail
  • Aldrich

  • (F20009)  Furfurylamine  ≥99%

  • 617-89-0

  • F20009-5G

  • 98.28CNY

  • Detail
  • Aldrich

  • (F20009)  Furfurylamine  ≥99%

  • 617-89-0

  • F20009-100G

  • 230.49CNY

  • Detail

617-89-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name furan-2-ylmethanamine

1.2 Other means of identification

Product number -
Other names 2-Furanmethylamine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Intermediates
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:617-89-0 SDS

617-89-0Synthetic route

furfural
98-01-1

furfural

furan-2-ylmethanamine
617-89-0

furan-2-ylmethanamine

Conditions
ConditionsYield
With ammonia; hydrogen In tetrahydrofuran at 80℃; for 2h; Autoclave;100%
With ammonia; hydrogen In methanol at 30℃; for 24h; Autoclave;91%
With ammonium hydroxide; Ni6AlO(z); hydrogen at 100℃; under 3000.3 Torr; for 5h; Autoclave;90%
(2-furyl)methyl alcohol
98-00-0

(2-furyl)methyl alcohol

furan-2-ylmethanamine
617-89-0

furan-2-ylmethanamine

Conditions
ConditionsYield
With ammonia In toluene at 100℃; under 5250.53 Torr; for 20h; Reagent/catalyst;94%
With ammonia; hydrogen In tetrahydrofuran at 180℃; for 60h; Autoclave;81.8%
With ammonia In tetrahydrofuran; dodecane at 180℃; under 3000.3 Torr; for 12h; Reagent/catalyst; Autoclave; Sealed tube; Inert atmosphere;43.1%
N-(furan-2-ylmethyl)formamide
72693-10-8

N-(furan-2-ylmethyl)formamide

furan-2-ylmethanamine
617-89-0

furan-2-ylmethanamine

Conditions
ConditionsYield
With caesium carbonate In methanol at 60℃; for 6h;94%
furfural
98-01-1

furfural

A

bis((furan-2-yl)methyl)amine
18240-50-1

bis((furan-2-yl)methyl)amine

B

furan-2-ylmethanamine
617-89-0

furan-2-ylmethanamine

Conditions
ConditionsYield
With ammonium hydroxide; 5% rhodium on activated aluminium oxide; hydrogen at 80℃; under 15001.5 Torr; for 3h; Reagent/catalyst; Temperature; Pressure; Autoclave;A 8.3%
B 91.7%
With ammonia; hydrogen In methanol at 100℃; under 22502.3 Torr; for 0.25h; Autoclave; Green chemistry;A 20%
B 44%
With ethanol; ammonia; nickel at 40 - 75℃; under 73550.8 Torr; Hydrogenation;
2-furaldehyde oxime
1121-47-7

2-furaldehyde oxime

furan-2-ylmethanamine
617-89-0

furan-2-ylmethanamine

Conditions
ConditionsYield
With borohydride exchange resin; nickel diacetate In methanol at 25℃; for 18h;84%
With hydrogenchloride In ethanol at 20℃; electroreduction at mercury cathode;75%
Stage #1: 2-furaldehyde oxime With hydrogenchloride In ethanol; water at 20℃; for 0.25h;
Stage #2: With zinc In ethanol; water for 1h; Reflux;
Stage #3:
70%
furfural
98-01-1

furfural

A

furan-2-ylmethanamine
617-89-0

furan-2-ylmethanamine

B

C10H11NO2

C10H11NO2

Conditions
ConditionsYield
With ammonium hydroxide; hydrogen In ethanol at 130℃; under 7500.75 Torr; for 12h; Autoclave;A 81.8%
B 9.1%
furfural
98-01-1

furfural

A

(2-furyl)methyl alcohol
98-00-0

(2-furyl)methyl alcohol

B

furan-2-ylmethanamine
617-89-0

furan-2-ylmethanamine

Conditions
ConditionsYield
With ammonia; hydrogen In tetrahydrofuran at 80℃; for 2h; Autoclave;A 19.3%
B 80.7%
Stage #1: furfural With platinum on carbon; ammonia In water for 1h; Green chemistry;
Stage #2: With hydrogen In water at 80℃; under 15001.5 Torr; for 2h; Green chemistry;
A 71.5 %Chromat.
B 26.9 %Chromat.
With ammonium hydroxide; platinum on activated charcoal; hydrogen at 80℃; under 15001.5 Torr; for 3h; Autoclave;
(4-{tris[2-(perfluorohexyl)ethyl]silyl}benzyl) furfurylcarbamate

(4-{tris[2-(perfluorohexyl)ethyl]silyl}benzyl) furfurylcarbamate

furan-2-ylmethanamine
617-89-0

furan-2-ylmethanamine

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In methanol at 20℃; for 16h;80%
2-(furan-2-ylmethyl)isoindoline-1,3-dione
4667-83-8

2-(furan-2-ylmethyl)isoindoline-1,3-dione

furan-2-ylmethanamine
617-89-0

furan-2-ylmethanamine

Conditions
ConditionsYield
With hydrazine hydrate In 1,4-dioxane at 110℃; Gabriel Amine Synthesis; Inert atmosphere;78%
furfural
98-01-1

furfural

A

N-furfurylidenefurfurylamine
19377-82-3

N-furfurylidenefurfurylamine

B

furan-2-ylmethanamine
617-89-0

furan-2-ylmethanamine

C

2,4,5-tris(2-furyl)imidazoline
550-23-2

2,4,5-tris(2-furyl)imidazoline

Conditions
ConditionsYield
With ammonia; hydrogen In methanol at 100℃; under 22502.3 Torr; for 0.25h; Reagent/catalyst; Autoclave; Green chemistry;A 7%
B 76%
C 8%
2-furancarbonitrile
617-90-3

2-furancarbonitrile

furan-2-ylmethanamine
617-89-0

furan-2-ylmethanamine

Conditions
ConditionsYield
With [Ru(H)(BH4)(CO)(PPh3)(3-(di-tert-butylphosphino)-N-((1-methyl-1H-imidazol-2 yl)methyl)propylamine)]; hydrogen In isopropyl alcohol at 150℃; for 3h; Inert atmosphere; Autoclave;75%
With ammonia; hydrogen In water; isopropyl alcohol at 110℃; under 15001.5 Torr; for 24h; Autoclave;73%
With [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); potassium tert-butylate; hydrogen; N,N'-dimesityl-4,5-dihydro-1H-imidazolium tetrafluoroborate In toluene at 80℃; under 26252.6 Torr; for 1h; chemoselective reaction;28 %Chromat.
(4-Methoxy-benzothiazol-2-yl)-carbamic acid tert-butyl ester
383866-35-1

(4-Methoxy-benzothiazol-2-yl)-carbamic acid tert-butyl ester

A

1-Furan-2-yl-methyl-3-(4-methoxy-7-phenyl-benzothiazol-2-yl)-urea

1-Furan-2-yl-methyl-3-(4-methoxy-7-phenyl-benzothiazol-2-yl)-urea

B

furan-2-ylmethanamine
617-89-0

furan-2-ylmethanamine

Conditions
ConditionsYield
A 66%
B n/a
furfural
98-01-1

furfural

A

TETRAHYDROFURFURYLAMINE
4795-29-3

TETRAHYDROFURFURYLAMINE

B

furan-2-ylmethanamine
617-89-0

furan-2-ylmethanamine

Conditions
ConditionsYield
With ammonia; hydrogen In tetrahydrofuran at 180℃; for 12h; Autoclave;A 40.7%
B 53.8%
With ammonia; hydrogen In methanol at 100℃; under 22502.3 Torr; for 0.25h; Autoclave; Green chemistry;A 34%
B 49%
With ethanol; ammonia; nickel at 180℃; under 73550.8 Torr; Hydrogenation;
2-furaldehyde oxime
1121-47-7

2-furaldehyde oxime

A

furan-2-ylmethanamine
617-89-0

furan-2-ylmethanamine

(±)-1,2-di(furan-2-yl)ethane-1,2-diamine

(±)-1,2-di(furan-2-yl)ethane-1,2-diamine

C

(1S,2R)-1,2-Di-furan-2-yl-ethane-1,2-diamine

(1S,2R)-1,2-Di-furan-2-yl-ethane-1,2-diamine

Conditions
ConditionsYield
With methanesulfonic acid; zinc In acetonitrile at 25℃; reduction;A 50%
B n/a
C n/a
With titanium tetrachloride; zinc In tetrahydrofuran at 25℃; reduction;A 3%
B n/a
C n/a
furfural
98-01-1

furfural

A

TETRAHYDROFURFURYLAMINE
4795-29-3

TETRAHYDROFURFURYLAMINE

B

N-furfurylidenefurfurylamine
19377-82-3

N-furfurylidenefurfurylamine

C

furan-2-ylmethanamine
617-89-0

furan-2-ylmethanamine

Conditions
ConditionsYield
With 0.5% Ru/activated carbon; ammonia; hydrogen In methanol at 100℃; under 22502.3 Torr; for 0.25h; Autoclave; Green chemistry;A 6%
B 8%
C 40%
(1E,2E)-1,2-bis(furan-2-ylmethylene)hydrazine
5428-37-5

(1E,2E)-1,2-bis(furan-2-ylmethylene)hydrazine

A

furan-2-ylmethanamine
617-89-0

furan-2-ylmethanamine

(±)-1,2-di(furan-2-yl)ethane-1,2-diamine

(±)-1,2-di(furan-2-yl)ethane-1,2-diamine

C

(1S,2R)-1,2-Di-furan-2-yl-ethane-1,2-diamine

(1S,2R)-1,2-Di-furan-2-yl-ethane-1,2-diamine

Conditions
ConditionsYield
With methanesulfonic acid; zinc In tetrahydrofuran at 25℃; for 8h; reduction;A 37%
B n/a
C n/a
With titanium tetrachloride; zinc In tetrahydrofuran at 25℃; for 8h; reduction;A 11%
B n/a
C n/a
5-hydroxymethylfuran-2-ylmethylamine
88910-22-9

5-hydroxymethylfuran-2-ylmethylamine

A

(2-furyl)methyl alcohol
98-00-0

(2-furyl)methyl alcohol

B

(furan-2,5-diyl) dimethanamine
2213-51-6

(furan-2,5-diyl) dimethanamine

C

furan-2-ylmethanamine
617-89-0

furan-2-ylmethanamine

Conditions
ConditionsYield
With ammonia In tetrahydrofuran; dodecane at 200℃; under 3000.3 Torr; for 12h; Autoclave; Sealed tube; Inert atmosphere;A 15.2%
B 25.4%
C 11%
furfural
98-01-1

furfural

A

N-furfurylidenefurfurylamine
19377-82-3

N-furfurylidenefurfurylamine

B

furan-2-ylmethanamine
617-89-0

furan-2-ylmethanamine

Conditions
ConditionsYield
With ammonia; hydrogen In methanol at 80℃; under 15001.5 Torr; for 2h; Autoclave; Green chemistry;A 17%
B 22%
With Runano/TiO2; ammonia; hydrogen In methanol at 89.84℃; under 30003 Torr; for 4h;A 7 %Chromat.
B 72 %Chromat.
With ammonium hydroxide; hydrogen In methanol under 750.075 Torr; for 12h; Autoclave; Heating;A 10.2 %Chromat.
B 88.4 %Chromat.
(2-furyl)methyl alcohol
98-00-0

(2-furyl)methyl alcohol

A

Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

B

furan-2-ylmethanamine
617-89-0

furan-2-ylmethanamine

Conditions
ConditionsYield
With ammonia In tetrahydrofuran; dodecane at 180℃; under 3000.3 Torr; for 12h; Autoclave; Sealed tube; Inert atmosphere;A 5%
B 13.8%
2-furancarbonitrile
617-90-3

2-furancarbonitrile

A

bis((furan-2-yl)methyl)amine
18240-50-1

bis((furan-2-yl)methyl)amine

B

furan-2-ylmethanamine
617-89-0

furan-2-ylmethanamine

Conditions
ConditionsYield
With ammonia; nickel Hydrogenation;
2-furaldehyde oxime
1121-47-7

2-furaldehyde oxime

A

bis((furan-2-yl)methyl)amine
18240-50-1

bis((furan-2-yl)methyl)amine

B

furan-2-ylmethanamine
617-89-0

furan-2-ylmethanamine

Conditions
ConditionsYield
With acetic acid; zinc
With ethanol; nickel Hydrogenation;
furfural phenylhydrazone
2216-75-3

furfural phenylhydrazone

ethanol
64-17-5

ethanol

sodium ethanolate
141-52-6

sodium ethanolate

A

furan-2-ylmethanamine
617-89-0

furan-2-ylmethanamine

B

aniline
62-53-3

aniline

hydrofuramide
494-47-3

hydrofuramide

A

bis((furan-2-yl)methyl)amine
18240-50-1

bis((furan-2-yl)methyl)amine

B

furan-2-ylmethanamine
617-89-0

furan-2-ylmethanamine

Conditions
ConditionsYield
With ethanol; nickel at 40 - 75℃; under 73550.8 Torr; Hydrogenation;
Brenzschleimsaeurenitril
72667-24-4

Brenzschleimsaeurenitril

furan-2-ylmethanamine
617-89-0

furan-2-ylmethanamine

Conditions
ConditionsYield
With sulfuric acid; zinc
furan-2-carbaldehyde oxime
620-03-1

furan-2-carbaldehyde oxime

furan-2-ylmethanamine
617-89-0

furan-2-ylmethanamine

Conditions
ConditionsYield
With sodium amalgam; ethanol; acetic acid
With tetramethylammonium bromide Mechanism; polarographic reduction at pH=3, other supporting electrolytes; values of diffusion current constant;
N-Furan-2-ylmethyl-N'-(4-nitro-phenyl)-formamidine

N-Furan-2-ylmethyl-N'-(4-nitro-phenyl)-formamidine

A

furan-2-ylmethanamine
617-89-0

furan-2-ylmethanamine

B

p-nitroformanilide
16135-31-2

p-nitroformanilide

Conditions
ConditionsYield
With water; acetic acid In tetrahydrofuran Ambient temperature; Yield given;
2-Furan-2-ylmethyl-1,1,1,3,3,3-hexamethyl-disilazane
94807-36-0

2-Furan-2-ylmethyl-1,1,1,3,3,3-hexamethyl-disilazane

furan-2-ylmethanamine
617-89-0

furan-2-ylmethanamine

Conditions
ConditionsYield
With toluene-4-sulfonic acid In methanol Heating;
anti-furfuraldoxime
1450-58-4

anti-furfuraldoxime

furan-2-ylmethanamine
617-89-0

furan-2-ylmethanamine

Conditions
ConditionsYield
With tetramethylammonium bromide Mechanism; polarographic reduction at pH=3, other supporting electrolytes; values of diffusion current constant;
furfurol-phenylhydrazone

furfurol-phenylhydrazone

furan-2-ylmethanamine
617-89-0

furan-2-ylmethanamine

Conditions
ConditionsYield
With sodium amalgam; ethanol; acetic acid

617-89-0Relevant articles and documents

-

Reeve,Christian

, p. 860 (1956)

-

Selective catalysis for the reductive amination of furfural toward furfurylamine by graphene-co-shelled cobalt nanoparticles

Liu, Jianguo,Ma, Longlong,Zhong, Shurong,Zhuang, Xiuzheng

, p. 271 - 284 (2022/01/19)

Amines with functional groups are widely used in the manufacture of pharmaceuticals, agricultural chemicals, and polymers but most of them are still prepared through petrochemical routes. The sustainable production of amines from renewable resources, such as biomass, is thus necessary. For this reason, we developed an eco-friendly, simplified, and highly effective procedure for the preparation of a non-toxic heterogeneous catalyst based on earth-abundant metals, whose catalytic activity on the reductive amination of furfural or other derivatives (more than 24 examples) proved to be broadly available. More surprisingly, the cobalt-supported catalyst was found to be magnetically recoverable and reusable up to eight times with an excellent catalytic activity; on the other hand, the gram-scale tests catalyzed by the same catalyst exhibited the similar yield of the target products in comparison to its smaller scale, which was comparable to the commercial noble-based catalysts. Further results from a series of analytical technologies involving XRD, XPS, TEM/mapping, and in situ FTIR revealed that the structural features of the catalyst are closely in relation to its catalytic mechanisms. In simple terms, the outer graphitic shell is activated by the electronic interaction as well as the induced charge redistribution, enabling the easy substitution of the –NH2 moiety toward functionalized and structurally diverse molecules, even under very mild industrially viable and scalable conditions. Overall, this newly developed catalyst introduces the synthesis of amines from biomass-derived platforms with satisfactory selectivity and carbon balance, providing cost-effective and sustainable access to the wide applications of reductive amination.

Synthesis of amides and esters containing furan rings under microwave-assisted conditions

Janczewski, ?ukasz,Zieliński, Dariusz,Kolesińska, Beata

, p. 265 - 280 (2021/03/17)

In this work, we present a novel method for the synthesis of ester and amide derivatives containing furan rings (furfural derivatives) under mild synthetic conditions supported by microwave radiation. N-(Furan-2-ylmethyl)furan-2-carboxamide and furan-2-ylmethyl furan-2-carboxylate were produced using 2-furoic acid, furfurylamine, and furfuryl alcohol. The reactions were carried out in a microwave reactor in the presence of effective coupling reagents: DMT/NMM/TsO? or EDC. The reaction time, the solvent, and the amounts of the substrates were optimized. After crystallization or flash chromatography, the final compounds were isolated with good or very good yields. Our method allows for the synthesis of N-blocked amides using N-blocked amino acids (Boc, Cbz, Fmoc) and amine. As well as compounds with a monoamide and ester moiety, products with diamides and diester bonds (N,N-bis(furan-2-ylmethyl) furan-2,5-dicarboxamide, bis(furan-2-ylmethyl) furan-2,5dicarboxylate, and furan-3,4-diylbis(methylene) bis(furan-2-carboxylate)) were synthesized with moderate yields in the presence of DMT/NMM/TsO– or EDC, using 2,5-furan-dicarboxylic acid and 3,4-bis(hydroxymethyl)furan as substrates.

Comparative account of catalytic activity of Ru- and Ni-based nanocomposites towards reductive amination of biomass derived molecules

Bhanage, Bhalchandra M.,Gokhale, Tejas A.,Raut, Amol B.

, (2021/06/18)

This work includes an effective comparison of metallic ruthenium and nickel nanoparticles loaded on montmorillonite clay (MMT) for reductive amination reaction of biomass-derived molecules. It comprises an eco-friendly reaction using water as a solvent, utilizing molecular hydrogen and liquor ammonia (25% aq. solution) for the synthesis of primary amines from bio-derived aldehydes within 3–10 h of reaction time. Various parameters such as temperature, hydrogen pressure, substrate/ammonia concentration ratio, and reaction time were optimized while comparing the selectivity of primary amines for both catalysts. The applicability scope of these catalysts was explored with a library of aryl and heterocyclic aldehydes. The reductive amination of crude furfural extracted from biomass feedstock (rice husk) and pure xylose sugar was tested, showing yields in the range of 11–36%, to show the wider industrial scope of both nanocomposites. Gram scale conversion was also carried out to showcase the bulk scalability of the Ru/MMT catalyst.

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